Everyone has an opinion on what makes a difference and what doesnt. I partially agree with some of what has been said already,though I have no personal experience with your Cipher cable.
"Upgrading" to a desktop DAC in the price range youre talking about may,or may not bring an audible difference. I know many members who have a/b'd various DACs in the 300.00-1000.00 price range and claim to not hearing a difference between them. Same members then heard a very costly DAC and were stunned at the differences.
I have personally owned several amps and DACs,and can clearly hear differences between them all.
The difference between the multibit and non-MB Schiit gear essentially is the MB versions have a warmer,more organic sound to them,whereas the non-MB can sound brighter and more digital. If youve never owned a high end turntable,then your ears are probably more used to the digital sound.
Its been my experience that everything makes a difference in your system,from the headphones down to the cabling,and everything in between,but as was mentioned above,its a slippery slope.